The present invention relates to an asymmetric producing method, and particularly a method of producing an optically active .beta.-hydroxy sulfonic acid compound by catalytic asymmetric hydrogenation.
.beta.-Hydroxy sulfonic acid compounds are among the important substances widely utilized in chemical industry and life science fields. For example, they are utilized as lubricants in electroplating of copper and Sn--Zn alloys and electrolytic pigmentation coating of aluminum, as stabilizers of disperse dyes, and as surface active ingredients of household cleansers. They also have high utility value as acid catalysts. Further, they attract attention in development of medicines based upon enzyme antagonism, since the sulfonyl group with a tetrahedrally arranged sp.sup.3 sulfur atom antagonizes with carboxyl groups. Development of practical method of providing optically active compounds is required, since difference in chirality changes molecular assembly forms and greatly influence interface and bulk properties or characteristics and extent of biological activities.
Previously, reactions of epoxides or 1-chloro-2-alkanols with sodium sulfite and reduction of .beta.-keto sulfonic acid compounds with metal hydrides have been reported as a method of producing a .beta.-hydroxy sulfonic acid compound.
However, these previous methods described above can not form an optically active .beta.-hydroxy sulfonic acid compound.